Triethylamine → tert-butyl N-[(2S)-1-hydroxybutan-2-yl]carbamate

HRID 2407880Notes

Reaction equation

HRID 2407880 reaction equation
[NH2:1][C@@H:2]([CH2:5][CH3:6])[CH2:3][OH:4].[C:7](=O)([O:13]C(C)(C)C)[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].C(N(CC)CC)C>C1COCC1>[OH:4][CH2:3][C@@H:2]([NH:1][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1200842-Amino-1-butanol, (+)-HCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 11263954tert-butyl N-[(2S)-1-hydroxybutan-2-yl]carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-2-aminobutan-1-ol (1 eq) in THF (0.26 M) at 0° C. was added di-tert-butyl carbonate (1 eq) and triethylamine (1 eq). The reaction was stirred at room temperature for 3 hours. The reaction mixture was concentrated en vaccuo; and the residue was diluted in ethyl acetate. The organic solution was washed with water (2×), brine, dried over anhydrous MgSO4, and concentrated en vaccuo. The material was carried onto the next step without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated en vaccuo
  2. additionand the residue was diluted in ethyl acetate
  3. washThe organic solution was washed with water (2×), brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated en vaccuo
  6. customThe material was carried onto the next step without further purification

Sources & evidence

ORD record
ord-1459a887427a47edb4a55289a5ba02bb
Source dataset
uspto-grants-2014_08
Patent number
US08808703B2

Reaction notes

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